Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury (Ep. 25)

Nine years of remote work, two layoffs over video calls, and a journey from Jamaican radio journalist to Foundpreneur — Stephen Stanbury has seen it all, and he's not holding back.Stephen Stanbury went from getting a letter of termination two months into his first job to becoming a Director of Operations at a fully remote company — all built on grit, Fiverr voiceovers recorded from his closet, and a refusal to let his Caribbean location be a ceiling. In this episode, Stephen unpacks what the remote work landscape really looks like in 2026, what mistakes Caribbean professionals keep making, and why your LinkedIn profile might be the most important job application you never sent. He also shares the story behind his new venture, Foundpreneur — a platform dedicated to spotlighting Caribbean entrepreneurs on a global stage.What we cover:How Stephen went from freelancing on Fiverr (using his company's internet) to Director of Operations — and what it really takes to climb in remote workWhy your LinkedIn profile, personal brand, and AI searchability are now more important than your resumeHow to stand out in a global applicant pool when everyone has an AI-optimised CVThe Caribbean Remote Work Conference 2026 — and why you need to be thereReady to build your remote career on your own terms? Head to theremoteislander.com for resources, episode notes, and more.Guest: Stephen Stanbury — Remote Work Veteran, Personal Branding Strategist, and Founder of Foundpreneur | Find him on LinkedIn: https://www.linkedin.com/in/stephenstanberry/You can find all of our links here:https://linktr.ee/theremoteislanderLinks mentioned:BairesDevKeron Rose's BlogEF SET 15-minute test*Edit: Payoneer has stopped its referral program but you can sign up for an account here.